Potassium Carbonate → HCID 59242991, compound

HRID 1644620Notes

Reaction equation

HRID 1644620 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 239344Methyl 3-hydroxy-5-nitrobenzoate

Product 1

HCID 59242991HCID 59242991, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a clean, dry 100 mL round bottom flask is added methyl 3-hydroxy-5-nitrobenzoate (240a, 0.4 g, 2 mmole, 1 eq), orthofluorobenzyl bromide (0.57 g, 3 mmole, 1.5 eq), potassium carbonate (0.56 g, 4 mmole, 2 eq), and DMF (3 mL). The reaction mixture was stirred at room temperature for 18 h and quenched with water and ethyl acetate. The product was extracted into the organic layer, dried over magnesium sulfate, filtered and evaporated. A white solid was obtained (0.49 g, 80% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.41 (s, 1H), 8.09 (s, 1H), 8.00 (s, 1H), 7.59 (dt, 1H, J=1.8, 8.0 Hz), 7.42 (m, 1H), 7.24 (dt, 1H, J=1.0, 8.0 Hz), 7.22 (dt, 1H, J=1.3, 8.0 Hz), 5.33 (s, 2H), 3.98 (s, 3H). Calc'd for C15H12FNO5; m/z (M+H+)=306; found 306.

Workup

  1. customTo a clean, dry 100 mL round bottom flask
  2. customquenched with water and ethyl acetate
  3. extractionThe product was extracted into the organic layer
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customA white solid was obtained (0.49 g, 80% yield)

Sources & evidence

ORD record
ord-272740001d504d2f923e059398d7a9d9
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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